Potassium Nitrate → 2-Chloro-4-fluoro-5-methyl-3-nitrobenzoic acid

HRID 369243Notes

Reaction equation

HRID 369243 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N+:13]([O-])([O-:15])=[O:14].[K+]>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:10]([N+:13]([O-:15])=[O:14])=[C:9]([F:11])[C:8]([CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 23284674Benzoic acid, 2-chloro-4-fluoro-5-methyl-

Product 1

HCID 232847252-Chloro-4-fluoro-5-methyl-3-nitrobenzoic acidYield 91%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

2-Chloro-4-fluoro-5-methylbenzoic acid (2.0 g) was added to concentrated sulfuric acid (20 ml) to dissolve it, and potassium nitrate (1.07 g) was added portionwise to the solution under ice cooling. After the addition, the temperature of the reaction mixture was given back to room temperature to conduct stirring overnight. The reaction mixture was poured into ice water and extracted with diethyl ether. After an organic layer was collected and dried over anhydrous magnesium sulfate, the solvent was distilled off to obtain the title compound (2.25 g) as a reddish brown oil.

Workup

  1. additionwas added portionwise to the solution under ice cooling
  2. additionAfter the addition
  3. customwas given back to room temperature
  4. extractionextracted with diethyl ether
  5. customAfter an organic layer was collected
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-7734ae73e96846fc8d9d7bda4d119a84
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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